Oh boy... where do I start. This hobby, just like racing, is a slippery slope. Here's an old photo of the SUV I bought bone stock to carry mountain bikes and a boat with: 
It now has a snorkel, too, because project creep.
First off, unless you're willing to put a chain around a wheel (scratches
) or buy an adapter, there's no place to jack a new Cherokee with a Hi-Lift. Maybe off of one of the front tow hooks, but I wouldn't bet on that. Modern cars just don't have much to grab, and they are very circular so the jack top usually hits the door, anyway. Farm jacks can be tricky if you've never used one before, too–I'd avoid that.
Self-recovery isn't that tough, and it's a necessary skill to learn. Learn it now, while you have a stock truck that can't get stuck too badly, and work your way up to the hard stuff. Otherwise, you'll probably have to learn it in the dark in your Jeep on 44s stuck in 8 feet of mud upside down.
Necessary tools for basic self-recovery:
Level 1:
Shovel.
Level 2:
Hi-Lift
sand ladders, boards, carpet, something to put under the wheel for traction.
Level 3:
Come-along with straps.
Level 4:
Winch
Level 5:
snatch blocks, anchors, etc.
If you do wade with it (I wouldn't, unless you're willing to change all the fluids), go slow, but still fast enough to make a bit of a bow wave. And don't stop. And if you do stop, don't open your door–crawl out the window.
Watch your rocker panels–I think the Trailhawk has skid plates, but your rockers are still very vulnerable. That has a locker in the back, too, so the drivetrain can probably write checks that the body can't cash.
Definitely go with somebody. Try self-recovery, then if you fail get them to tow you out, and try again.
A good rule of thumb for supplies, tools, etc. is to assume that the truck will disappear at your furthest point from civilization. If you can walk back from there, bring boots and water and food. If you can't, bring lots of tools, and enough gear to comfortably spend the night. Look at a coverage map and see if you'll have cell. If it's at all iffy, then leave somebody you know a piece of paper that says "I will be going to X, at X time via X route. If I don't check in with you by X, please send help."
It's intimidating, but you'll have a lot of fun and it's well worth it.
Oh, one more thing: though they aren't great, pretty much every club uses CB radios to communicate. Put one in your Jeep if you're going with anybody else.
Oh, and let your tires down to 15 psi or so. That will give you more traction.
